反应详情

温度

-78 °C

A solution of {[(3-bromophenyl)methyl]oxy}(dimethyl)silane-2,2-dimethylpropane (1:1) (100.0 g, 331.9 mmol) in THF (500 mL) was cooled to −78 C, and then n-BuLi (132.7 mL, 331.9 mmol) was added dropwise. The mixture was stirred for 1 h at −78° C. Then B(OBu)3 (107.5 mL, 398.2 mmol) was added in one portion. The reaction mixture was warmed to room temperature, and stirred over night. After cooling to 0° C., 5% H3PO4 was added to pH=4-5 and the mixture stirred 0.5 h and then filtered. After removing THF, the residue was extracted with Et2O (200 mL×2), and the organic layer was dried over Na2SO4. After removing the solvent, the residue was added to water, and a white solid precipitated which was dried in vacuo to give 65.7 g of [3-({[(1,1-dimethylethyl)-(dimethyl)silyl]oxy}methyl)phenyl]boronic acid (yield: 74.5%). 1H NMR (400 MHz, CDCl3) δ 0.14 (s, 6H), 0.98 (s 9H), 4.88 (s, 2H), 7.49-7.59 (m, 2H), 8.14 (d, J=7.6 Hz, 1H), 8.19 (s, 1H).

1. temperatureThe reaction mixture was warmed to room temperature
2. stirringstirred over night
3. temperatureAfter cooling to 0° C.
4. stirringthe mixture stirred 0.5 h
5. filtrationfiltered
6. customAfter removing THF
7. extractionthe residue was extracted with Et2O (200 mL×2)
8. dry with materialthe organic layer was dried over Na2SO4
9. customAfter removing the solvent
10. additionthe residue was added to water
11. customa white solid precipitated which
12. customwas dried in vacuo